Process for dyeing textile material of mixtures of polyester and cellulose fibers

ABSTRACT

Textile materials consisting of mixtures of polyester and cellulose fibers are dyed equal shades by (a) impregnation with an alkaline solution containing a coupling component, and wetting or dispersing agents, (b) drying the material, (c) impregnation with an acid solution containing a diazotized aromatic or heterocyclic amine and a disperse dye, (d) drying the material and (e) subjecting it to a heat treatment.

United States Patent Lowenfeld et al.

[4 Feb. 15, 1972 PROCESS FOR DYEING TEXTILE MATERIAL OF MIXTURES OFPOLYESTER AND CELLULOSE FIBERS lnventors: Rudolf Lowenfeld, Buchschlag;Uwe Kosubek, Offenbach/Main, both of Germany Assignee: Farbwerke HoechstAktiengesellschaft vormals Meister Lucius & Bruning, Frankfurt/Main,Germany Filed: July 7, 1969 Appl. No.2 839,647

Foreign Application Priority Data July 11, 1968 Germany ..P 17 69 775.5

Int. Cl. ..D06p 3/82 Field of Search ..8/2l

References Cited UNITED STATES PATENTS 12/1968 Fono et al. ..8/2l COTHER PUBLICATIONS llg Mell. Text 111)., 2/1963, p. ]76|79, EnglishTrans].

Ab J. Soc. Dyers & Colorists, 6/1963, 278 AM. D. Rep..

Wygand, 12-7-1964, p. 106-109 Primary ExaminerGeorge F. Lesmes AssistantExaminer-Patricia C. lves AtrorneyConnol1y and Hutz [5 7] ABSTRACT 5Claims, No Drawings PROCESS FOR DYEING TEXTILE MATERIAL OF MIXTURES OFPOLYESTER AND CELLULOSE FIBERS The present invention provides a processfor dyeing textile material of mixtures of polyester and cellulosefibers.

lt is already known that textile material consisting of mixtures ofpolyester and cellulose fibers may be dyed fast shades, using dispersedyestuffs and water-insoluble azo dyestuffs produced on the fiber. Theprocess is carried out in such a manner that the portion of polyesterfiber is first dyed with disperse dyestuffs at boiling temperature, inthe presence of dyeing accelerators, under the conditions ofhigh-temperature dyeing or according to the so-called thermosol-process,and subsequently, the water-insoluble azo dyestuff is produced on thecellulose fiber portion by impregnation with a coupling component andsubsequent development with a diazotized aromatic amine. When theprocess is carried out in this manner, dyeings of good quality areobtained. However, it takes a long time as the disperse dyestuff, thecoupling component and the diazotized aromatic amine must each beapplied in separate dyeing baths.

it has now been found that it is possible to avoid this disadvantage inthe process of dyeing textile material of mixtures of polyester andcellulose fibers, by treating the textile material with alkalinesolutions containing a coupling component as well as wetting ordispersing agents, drying it, subsequently treating with acid solutioncontaining, in addition to compounds giving an acid reaction, adiazotized aromatic or heterocyclic amine as well as at least onedisperse dyestuff, drying and then subjecting it to a heat treatment.

According to the process of the invention the textile material, forexample blended fabrics of polyester and cellulose fibers, isimpregnated with an alkaline solution containing a coupling component aswell as wetting or dispersing agents, and it is then squeezed off anddried. During the process, the content of alkali in the impregnationbath must be such that the coupling component does not precipitate.Depending on the nature and the concentration of the coupling component,5 to 30 ml. of a 32.5 percent sodium hydroxide solution per liter ofwater are used as alkali. Subsequently, the textile material isimpregnated with a solution containing a compound giving an acidreaction, a diazotized primary aromatic or heterocyclic amine as well asa disperse dyestuff. The content of the compound giving an acid reactionmust be such that the alkali applied onto the textile material togetherwith the coupling component in the course of the alkaline impregnationis neutralized, and that the pH-value of the goods to be dyed still isbetween about 3 and 7. The disperse dyestuff is used in an amount suchthat the polyester fiber portion is dyed with approximately the sameintensity as the cellulose fiber portion. After the impregnation withthe acid developing bath containing the diazotized amine and thedisperse dyestuff, the textile material is squeezed off, dried andsubjected to a heat treatment at temperatures in the range offrom 170 to210 C. This heat treatment may be carried out with hot air or contactheat. Finally, the material is washed in an alkaline solution, rinsedand dried.

In the process of the invention, the water-insoluble azo dyestuffdevelops on the cellulose fiber portion when the material impregnatedwith the coupling component is brought into the acid developing bath.The disperse dyestufi is applied onto the material during the couplingat its passage through the developing bath, but it is only fixed in afast manner on the polyester fiber portion in the course of the heattreatment at temperatures in the range of from 1707 to 210 C. Thereby,the water-insoluble azo dyestuff is obtained in full yield andclearness. The dyeings obtained possess very good fastness properties.

As textile materials, there maybe used blends containing from aboutpercent of polyester'fiber and 75 percent of cellulose fiber to 70percent of polyester'fiber and percent of cellulose fiber.

Appropriate polyesterfibers are those made of aromatic 'po'lyesters,'forexample of =terephthalic acid or diphenyl-4,4'-

dicarboxylic acid and alkane diols or l,4-cyclohexanedimethanol, as wellas triacetyl cellulose. As cellulose fibers, native or regeneratedcellulose fibers may be used.

In the process of the invention, the coupling components which 1 enterinto consideration are especially aromatic ohydroxy-carboxylic acidarylamides or acylacetic acid aryla mides, such as, for example,2,3-hydroxynaphthoic acid arylamides, 6-bromo or6-alkoxy-2,3-hydroxynaphthoic acid arylamides or acetoacetic arylamideswhose substantivity with respect to cellulose fibers is weak to medium.When appropriate impregnation equipments are used, having for example asmall liquor reservoir, it is also possible to use coupling componentswhich have a high substantivity with respect to cellulose fibers, forinstance the condensation products of 2,3- hydroxynaphthoic acids withpolynuclear isocyclic or heterocyclic amines, such as aminonaphthalenes,aminocarbazoles or aminodiphenylene oxides, moreover heterocyclicohydroxy-carboxylic acid arylamides, for example,S-hydroxyl,2,l',2-benzocarbazole-4-carboxylic acid arylamides, 2-hydroxycarbazole-3-carboxylic acid arylamides, and 4,4'-bis-(acetoacetylamino)-diphenyls or Z-hydroxy-anthracene-llcarboxylic acidarylamides.

As diazotized primary aromatic or heterocyclic amines there may be takeninto consideration monoamines or diamines, for example diazotizedchloro-anilines, dichloroanilines, chloro-toluidines, chloro-anisidines,nitroanilines, nitrotoluidines, nitroanisidines, nitroxylidines,nitrophenetidines, cyanotoluidines, cyanoanisidines,aminobenzene-sulfonic acid amides, aminobenzene-carboxylic acid amides,aminophenyl alkyl-, arylor -aralkyl-sulfones, aminodiphenyl ethers,trifluoro-methyl anilines, monoacylated phenylenediamines,arninoazobenzenes or aminocarbazoles as well as tetrazotized4,4'-diamino-diphenyls.

As wetting or dispersing agents in the alkaline impregnation bath theremay be used especially condensation products of high-molecular-weightfatty acids and protein degradation products, condensation products ofhigh-molecular-weight fatty acids and aminoalkylsulfonic acids,condensation products of fonnaldehyde and naphthalene sulfonic acids aswell as purified waste lignin liquor.

The compounds giving an acid reaction in the developing bath are eitherorganic acids such as, for example, acetic acid, formic acid, propionicacid, lactic acid, glycolic acid, tartaric acid or citric acid, or saltsgiving an acid reaction such as, for example, monosodium phosphate oraluminum sulfate. When nonvolatile acid compounds are used, care must betaken that a quantity not higher than that required for theneutralization of the alkali applied onto the material is used. Anexcess amount of a nonvolatile acid compound might cause, during thesubsequent heat treatment, a damage of the cellulose fiber portion ofthe fabric.

As disperse dyestuffs, there may be used dyestuffs which, due to theirthermal properties, can be used in the so-called thermosol treatment,i.e., dyestuffs which dye polyester fibers at temperatures in the rangeof from to 210 C. and do not soil the coloring aggregates because of ahigh volatility. Suitable disperse dyestuffs of the azoand anthraquinoneseries are described in Color index Second Edition 1956, Vol. l, page1659-1742 and Supplement I963, p. 8179-5224, and in the correspondingAdditions and Amendments, No. 1, Sept. 1963 to No. l8,.lan. I968.

The process of the invention maybe carried out continuously orsemicontinuously.

With-respect to the known methods of working in which, in the firstoperating stage, the disperse dyestuff is fixed on the polyester fiberportion of the blended fabric by a thermosol treatment, the process ofthe invention allows the application of the disperse dyestuff to becombined with the manufacture of the water-insoluble azodystuff on thecellulose fiber portion of the blended fabric. in this manner, oneworking stage can be omitted.

The following examples illustrate the inventionybut they are notintended to limit it thereto, the parts and percentages beingby weight.

EXAMPLE l acid per liter of water. A full red dyeing with good fastnessA blended fabric consisting of 67 percent of a polyethylene Propertieswas obained' glycol terephthalate fiber and 33 percent of a cotton fiberwas The following table indicates a series of further couplingimpregnated with a solution containing, as per liter of water,components and diazo components to be used according to 16.6 g. of2,3-hydroxynaphthoylaminobenzene dissolved in 5 the invention, as wellas disperse dyestuffs and the shades obl6.6 ml. of sodium hydroxidesolution (32.5 percent) and hot tainable therefrom on mixed fabrics offibers of polyethylene water of 90 C., 4 g. of a condensation-product offormalglycol terephthalate (67 percent) and cotton (33 percent).

Coupling component Diazo component Disperse dyestufl Shade 2 3.] ydoxynaphthoylaminobenzcno 1'-amino-2-nitrel enzene 0.1. disperse orange13.. Orange. 1-(2',3-hydroxynephthoylemino)-2phlorobenzenel-itmine-3,E-bis-trilluoromothylbonzene- 0.1. disperse yellow-68.-Golden yellow. 1-(2,3'-hydroxynaphthoylamino)-4-ehlorobenzenel-amino4-ehloro-iZ-triiluoromethylbenzene. 0.1. disperse red 82 Blueishred. 1- 2',3'-h drex ne htho iemino)-2-methylhenzene.l-amino-l-chlorobenzeue 0.1. disperse orange 13.. Orange.1-(2,3'-hydroxynaphthoylamin0)-2-muth0xyb0t1zefl0.l-amino-B-ehlorobenzene do De,1-(2,3'-hydroxynaphthoylamino)-2-methylbenzenel-emino-Z-methyl-fi-nitrobenzene.0.1. disperse red 91 Red. 1-(2,3-hydroxynaphthoyiamino)-2-ethoxybenzene.1-arnino-2,5-dlmethoxyt-benzo-nitrlle.. 0.1. disperse red 90 Bordo. v1-(2',3-hydroxynaphthoylamino)-2-methylbenzenel-apiilinlo-rirgathoxybenzene-fi-sulionic acid di- C.I. disperse red 82Blueish red.

1-(2',3-hydr0xynaphthoylarnino)-2-meth0Xybel'1Zen6..1-amino-2-methy1-5-chlorobenzene 0.1. disperse red 91 Red.

Do 0.1. disperse red 90 Red. 1-(2',3'-hdr0xynaphthoylamino)-2-methylbenzene o do1-(2,3'-hydroxynaphthoylamino)-2-methyl-4-methoxyl-amino-2-methyl-4-ehlorobenzenede benzene. 1-(2',3-hydrexynaphtoylamine)-2,4-dimethoxy-5-chloro-1-amine-2methexy-E-chlorobenzene do Blueish red.

benzene. 2 3.hydroxvnaphthoylaminobenzene1-emino-4-bem.oylamine-2.5-diethoxybenzene. 0.1. disperse blue 81. Blue.1-(2',3'-h droxynaphthoylemino)-2-methoxybenzene.4,4-diamin0-3,3-dimethoxydipheny1 de Do, 2,3-hydroxynaphtoylaminobenzenc4-amin0-4-mei:hoxydiphenylamine. do Do.1-(2-liydroxyearbezol-3-earboylumino)-4-ohlorohenzcne.l-emino-Z-methyl-B-ehiorobenzene 0.1. disperse orange 13 Brown.

plus 0.1. disperse blue 66 plus 0.1. disperse red 82.1-(3-iiydrexydiphenyleneoxide-W-cerboylamino)-2,5- ..-..do 0.1. disperseorange 13 Do.

dimetlioxybonzene. plus 0.1 disperse blue 56drgl2us 0.1. disperse re1-(5-hydroxy-i,2,1,2"-benzocerbuzol-4 cerboylamin0)- 1-emin0-2-methoxy-4mitrobenzene 0.I. disperse blue 81 Black.

4-metl1oxybenzene plus 0.1. disperse orange 13 lus 0.1.

disperse re 82. 4,4-bis-acetoacetylamino-S,3dimethyl-d1phenyll-amino-Z-ehlorobenzene.... 0-I- disperse yellow 5 Yellow.Therephthlalloyl-his;(l-acetyl-aminoa-meth0Xy-4chl0r0-1-amino-2,fidichlorobenzene C.I. disperse yellow e3 Do.

5-metl1y enzene e-methoxy-2.3-hydroxynaphthoylaminobenzenel-amin0-2-methyl-5-chiorobenzene 0.1. disperse red 82 Bordo.

dehyde with B-naphthalenesulfonic acid and 0.5 g. of sodium 4 We claim:7 salt of 2,5-dibutylnaphthaline sulfonic acid. Subsequently the. 1. Ina process for dyeing textile materials consisting of mixfabric wasqueezed off until th li uor ab o ti h d tures of polyester andcellulose fibers by impregnating the texreached 60 percent of the drygoods weight, dried and imtile material with an alkaline solutioncontaining a coupling pregnated with a solution containing, per liter ofwater, 10.6 g. pf and Wemng f dlsperslllg drymg h of diazotizedl-amino-2-methyl-chlorobenzene, 21 ml. of a 50 "l f q lfl f p g fimaterial percem acetic acid, 10 g. f Sodium acetate, 3 f Cl with an acidsolution containing at least one disperse dyestuff Disperse Red 90, and2 g. of a condensation product of formaldehyde withB-naphthalenesulfonic acid. Subsequently, the fabric was squeezed offuntil the liquor absorption had reached 60 percent of the dry goodsweight and the fabric was I then passed through a drying aggregate to afixation chamber .S 3 l e fl ffla e i 9ibii te y qe ivfi' or over hotrollers in a manner such that it was heated to to obtain a pH from about3 to 7, drying the material and then subjecting this dried material toheat treatment ata temperature in the range of about 170 to 210 C., theimprovement which consists essentially of adding in the acidimpregnation 2. The process as claimed in claim 1 wherein the l80-2i0C.during 30 to 60 seconds. Finally, the fabric was component is anaromatic y yy acid y after-treated, at boiling temperature, with 2 g. ofa 30 percentamide an acylaceto amidereaction product of about 10 molesof ethylene oxide and l mole of nonyl phenol and 2 ml. of a 25 percentsolution of the sodium salt of nitrilotriacetoacetic acid per liter ofwater, and rinsed in hot and cold baths. The after-treatment of thedyeing could also be carried out, at temperatures in the range of fromto 95 C., in a bath containing 3 g. of a mixture consisting of 63percent of perchloroethylene, 17 percent of a reaction product of about10 moles of ethylene oxide and 1 mole of nonyl phenol and 20 percent ofisopropyl alcohol and 2 g. of a 25 percent solution of the sodium saltof nitrilotr iacet oacetic 65 compound is of the benzene, diphcnyl orcarbazole series.

dye is of the azo or anthraquinone series.

acid or a purified waste lignin liquor.

3. The process as claimed in claim 1, wherein the diazo 4. The processas claimed in claim 1, wherein the disperse 5. The process as claimed inclaim 1, wherein the wetting or 60 dispersing agent is a condensationproduct of a long-chain fatty acid and a protein degradation product oran aminoalkyl sulfonic acid or of formaldehyde and a naphthalenesulfonic

2. The process as claimed in claim 1, wherein the coupling component isan aromatic o-hydroxy-carboxylic acid aryl amide or an acylaceto arylamide.
 3. The process as claimed in claim 1, wherein the diazo compoundis of the benzene, diphenyl or carbazole series.
 4. The process asclaimed in claim 1, wherein the disperse dye is of the azo oranthraquinone series.
 5. The process as claimed in claim 1, wherein thewetting or dispersing agent is a condensation product of a long-chainfatty acid and a protein degradation product or an aminoalkyl sulfonicacid or of formaldehyde and a naphthalene sulfonic acid or a purifiedwaste lignin liquor.